3-bromopropyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside | 1112264-96-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-bromopropyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5S,6R)-2-(3-bromopropoxy)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 1112264-96-6
• 化学式: C₃₇H₄₁BrO₆
• 分子量: 661.633
• InChiKey: UCXWUCPYIBCAPD-WNRBQEJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-galactopyranoside 、 3-溴-1-丙醇 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到3-bromopropyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  [bmim][OTf]: a versatile room temperature glycosylation promoter

  摘要：

  [bmim][OTf] is a versatile, ionic liquid promoter for the room temperature glycosylation of both thiophenyl and trichloroacetimidate glycoside donors; the conditions are mild, with no requirement for molecular sieves, and are compatible with a wide range of donors and protecting groups. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.042

文献信息

• N-benzoylglycine/thiourea cooperative catalyzed stereoselective O-glycosidation: Activation of O-glycosyl trichloroacetimidate donors
  作者：Atul Dubey、Rekha Sangwan、Pintu Kumar Mandal

  DOI：10.1016/j.catcom.2019.04.006

  日期：2019.5

  A new practical utility for beta-stereoselective glycosylation via activation of O-glycosyl trichloroacetimidate donors using N-benzoylglycine/thiourea cooperative catalysis has been demonstrated. This method represents the first instance where amino acid derived N-benzoylglycine is used as a catalyst for O-glycosylation under mild reaction conditions at ambient temperature. NMR spectroscopy studies suggest that thiourea cocatalyst exhibit a cooperative behaviour that has a strong effect on the reaction rate, yield, and the beta-selectivity.
• [bmim][OTf]: a versatile room temperature glycosylation promoter
  作者：M. Carmen Galan、Claire Brunet、Monica Fuensanta

  DOI：10.1016/j.tetlet.2008.11.042

  日期：2009.1

  [bmim][OTf] is a versatile, ionic liquid promoter for the room temperature glycosylation of both thiophenyl and trichloroacetimidate glycoside donors; the conditions are mild, with no requirement for molecular sieves, and are compatible with a wide range of donors and protecting groups. (c) 2008 Elsevier Ltd. All rights reserved.